Cleve Jones can cite the exact moment when Sean Penn morphed into Harvey Milk.

It occurred during filming of a crucial scene in Gus Van Sant’s multiple-Oscar-nominated biopic “Milk,” which stars Penn as the former San Francisco supervisor, one of America’s first openly gay elected officials.

After honing his political skills as a flamboyantly courageous, bullhorn-toting community organizer, the so-called Mayor of Castro Street decided to run for office. He shed his aging-hippie couture, cut off his ponytail and took to wearing conservative suits, the better to reassure anxious Pacific Heights matrons that he was a serious candidate.

When Penn emerged on set one day in that incarnation, ready for filming, Jones was struck by the actor’s uncanny resemblance to his beloved friend and mentor.


“That was the day it all came together and Sean, like, had this direct line to Harvey,” says Jones, a longtime Bay Area gay rights and labor activist who served as a consultant on the movie and appears in three cameos, in addition to being portrayed in “Milk” by actor Emile Hirsch.

“It was weird,” Jones continues. “It was eerie and wonderful and at times just incredibly sad.”

Judging by the evidence of Oscar voting, a number of factors harmonically converged in the making of “Milk.” In Van Sant, the movie found a director capable of imparting a resolutely independent vision to a film that’s intended to play as well on Main Street as on Haight Street.

In Dustin Lance Black, it procured a screenwriter able to humanize and dramatize an opera-sized chapter of American social history.

And with such supporting actors as James Franco, Diego Luna and the Oscar-nominated Josh Brolin as Milk’s political rival and eventual assassin, Dan White, along with Danny Elfman’s inventive musical score, the filmmakers were able to conjure not only one man’s remarkable story but also the turbulent sensibility of a mind-blowing epoch.

Still, none of these contributions would’ve added up without a lead actor who could bring focus and verisimilitude to Milk’s ebullient, prismatic personality, an actor who could embody, rather than merely impersonate, the actual man.


Enter Sean Penn.

“I don’t think anything could’ve prepared us for what he brought to the screen,” says Bruce Cohen, who produced the movie with Dan Jinks.

“What we’ve heard from so many people is, you forget you’re watching Sean Penn,” Jinks concurs.

When White’s bullets struck down Milk and San Francisco Mayor George Moscone on Nov. 27, 1978, America lost not only one of its most intellectually nimble and socially progressive politicians, it also lost a man whom Jones calls “one of the most empathetic people I’ve ever met.” Among those who knew him best and worked with him most closely, Milk was cherished not only for his relentlessly determined leadership but for his wit, sensitivity and grace under pressure.

No one associated with the film doubted Penn’s ability to meet the role’s enormous technical demands -- indeed he is among the film’s Oscar nominees. Besides his professional credentials, he brought to the table other experiences as a political activist and occasional globe-hopping journalist that made him seem a natural fit to play Milk.

Van Sant says that during the casting process, he watched a number of YouTube videos showing Penn giving speeches at town hall meetings and in other forums, demonstrating his oratorical flair and charisma.

“I think a lot of it was aimed at Bush and the Iraq war,” Van Sant says. “He was funny, he was also daring and also accurate and extreme, which are a lot of things Harvey was. We were very inspired by his talks.”


As part of his research process, Black interviewed more than 40 people who had known Milk in various capacities. His screenplay provided Penn and the other actors with the foundations of authenticity on which to construct their roles.

“He and I talked about the ideas somewhat,” Van Sant says of Penn, who wasn’t available for interviews, “but I think he kind of assimilated his character through studying Harvey and using his imagination and willing it into being.”

Even so, certain aspects of Penn’s screen image and popular reputation might’ve appeared to be at odds with Milk’s persona.

“Maybe the surprise that Sean brings to it is because of his roster of characters being pretty macho,” Van Sant says. “That’s kind of an interesting turn.”

Jones acknowledges that, before meeting Penn, he “had this overall general impression” that “he was a blunt, possibly arrogant kind of a guy.” Then during an early phase of the filmmaking process, he and Penn were discussing how the actor intended to portray Milk. “He said, ‘I’m just going to play him as a kind man,’ ” Jones recalls. “I felt tremendously relieved at that point.”

Through working with Penn, Jones discovered him to be “a smart, generous, incredibly well-informed person” who possesses Milk’s quality of “empathy and genuine interest in other people” mixed with what Jones characterizes as a type of fearlessness. “I doubt Harvey was ever intimidated, and I don’t think Sean is either.”


During filming, by all accounts, the on-set atmosphere was highly amicable and relaxed. “There were no meltdowns, there were no raised voices, there were no egos on parade,” Jones says. The cast cultivated a true ensemble atmosphere befitting the cooperative spirit of Milk and his political entourage during the volatile late 1970s. “Something this article should say is, everybody took a tremendous pay cut to be part of this movie,” Jinks says.

Yet at times it was emotionally draining to relive those electric, traumatic years. “The first couple of weeks I was a blubbering idiot,” Jones says. Among the most difficult scenes to film was Milk’s killing. Jones, then 22, was one of the first people to discover Milk’s dead body, the first one that he’d ever seen. Watching that sequence “just about destroys me every time,” he says.

But if parts of Harvey Milk’s life and times were painful to reenact, the filmmakers share a sense of optimism that the movie has spurred renewed interest both in Milk and in the origins of the gay rights movement. With last fall’s passage of California’s controversial Proposition 8, many of the themes that “Milk” raises have acquired a reinvigorated relevancy.

“I tend to think in some ways it’s been timely the whole time,” Van Sant says. “But it’s timely this year as well.”

It may be especially well-timed for young people, including younger gays who’d never heard the story. Jones says that in recent years whenever he gave talks to students very few of them knew anything about Harvey Milk.

Now, he says, “I ask, ‘How many of you have seen the film?’ and everybody’s hand goes up.”





Power of penn

He’s often called the greatest actor of his generation, yet Sean Penn has only one Oscar. His performance as Harvey Milk in “Milk” marks his fifth nomination -- all for leading performances -- so, if the early award shows are any indicator, this could be his year to make a matched set.


2004: Lead actor for “Mystic River”


2009: Lead actor and shared the acting ensemble award for “Milk”

2004: Lead actor for “Mystic River”


2004: Lead actor in a dramatic film for “Mystic River”


1996: Male lead for “Dead Man Walking”


2009: Male lead for “Milk”